Now that they’ve bailed on their second marriages, fans are excited to see Jennifer Aniston and Brad Pitt rekindling the flame. Brad split from wife Angelina Jolie in 2016, and Jennifer confirmed her breakup with husband Justin Theroux in February. Of course, Brad and Jen had a lot of marriage drama of their own back in the day, not the least of which was Brad’s on-set romance with Angelina. But in honor of these O.G. spouses reconnecting, we’re recapping Jen and Brad’s relationship thus far with the timeline below.
1998: Jennifer Aniston and Brad Pitt Spotted Kissing for the First Time
1998: Brad and Jen start dating after being set up by their agents. (So Hollywood, right?)
They’re spotted kissing that June at the Tibetan Freedom Concert festival in Washington, D.C., but elsewhere they try to keep their relationship on the down-low, especially because Brad had weathered a very public breakup with Gwyneth Paltrow. “We just wanted to keep it special. Keep it ours,” he later told Rolling Stone.
September 1999: Brad and Jen make their public debut at the 51st Primetime Emmy Awards. (The Friends star goes on to take home her own Emmy three years later.)
November 1999: They’re engaged! Taking the stage at a Sting concert in New York City, Jennifer and Brad show off the diamond-and-platinum engagement ring he ordered for her from Italian jewelry designer Silvia Damiani — after he spent seven months planning the design.
2000: Brad Pitt and Jennifer Aniston’s Wedding Makes a (Pricey) Splash
July 2000: Brad and Jen tie the knot! It’s just your simple $1 million Malibu wedding with 200 guests, 50,000 flowers, a firework show, and a gospel choir.
As hairstylist Chris McMillan later told People, it was the perfect wedding for the bride. “I’ve known her a long time, and she and I would talk about the day she gets married,” he said. “There were big expectations, and this went way beyond that, way beyond. It was a great and happy day.”
August 2003: Angelina Jolie replaces Nicole Kidman as the Mrs. Smith to Brad’s Mr. Smith, spelling the beginning of the end of Brad and Jen’s marriage.
January 2004: Brad and Angelina start filming Mr. & Mrs. Smith. Angelina later told The New York Times, they “fell in love” on that set, and People later reported that Jennifer realized her husband’s head had been turned.
“Jennifer knows that Angelina got under his skin, and it bothered her,” a source told the magazine at the time. “They did not sleep with each other,” another source contended, “[But Brad] was obviously taken by Angelina.”
2005: Jennifer Aniston and Brad Pitt’s Last Vacation Together Ends in Divorce
January 2005: Just after a vacation to Cabo San Lucas, Mexico — during which they were photographed kissing on the beach — Brad and Jen announce their split via a joint statement.
“We would like to announce that after seven years together we have decided to formally separate,” they say. “For those who follow these sorts of things, we would like to explain that our separation is not the result of any speculation reported by the tabloid media. This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another.”
March 2005: Jennifer officially files for divorce from Brad, calling an end to their nearly-five-year marriage. (She cites “irreconcilable differences,” which is a funny way of spelling “Angelina Jolie.”)
2005: Brad Pitt Goes Public With Angelina Jolie Months After His Separation From Jen
April 2005: Photos of Brad on vacation with Angelina and her son Maddox in Kenya hit the press.
October 2005: The exes finally finalize their divorce, not long after Jennifer tells Oprah Winfrey she’s looking forward to her future, saying, “I love the discovery of what will be happening and just kind of sitting back and not knowing.”
December 2008: Jennifer tells Vogue she was annoyed by Angelina’s January 2007 interview with the same magazine, saying Angie’s GF shouldn’t have been so forthcoming about her and Brad’s flirtations.
“There was stuff printed there that was definitely from a time when I was unaware that it was happening,” Jennifer says. “I felt those details were a little inappropriate to discuss.” (She also admits to laughing about a New York Post cartoon depicting her taking Angelina up on her offer of a “sit-down” … while loading a shotgun. “The funniest thing I’ve ever seen,” she says.)
May 2011: Dating rumors spark between Jennifer and Justin Theroux, after the two are spotted together at The Tower Bar in West Hollywood.
August 2011: Justin and Jen move in together and make their relationship official.
February 2012: Jen opens up about her relationship with Justin. “Having experienced everything you don’t want in a partner over time, it starts to narrow down to what you actually do want,” she tells InStyle. “As I get older I realize what qualities are important in love and what suits me. And what I won’t settle for.”
April 2012: Brad and Angelina get engaged. “It is a promise for the future and their kids are very happy,” the couple tells People.
August 2012: Justin proposes to Jen, and his rep confirms their engagement with the following statement: “Justin Theroux had an amazing birthday on Friday, receiving an extraordinary gift when his girlfriend, Jennifer Aniston, accepted his proposal of marriage.”
August 2014: Brad and Angelina get married in France.
2015: Jennifer Aniston and Justin Theroux’s Wedding Ceremony Secretly Takes Place
August 2015: Jen and Justin have a secret wedding in the backyard of their Bel Air home. Jimmy Kimmel officiates the ceremony.
September 2016: Brad and Angelina file for divorce following a plane incident where Brad allegedly got in an altercation — which was investigated by the FBI — with his son Maddox. Brad and Angelina enter a custody battle — which ends up getting stalled for 18 months — over their six kids.
November 2017: Brad starts dating again. According to In Touch, Brad became smitten with a 21-year-old British actress named Ella Purnell. “Brad had Ella in mind from the get-go. He went out of his way to cast her,” a source explains. “Ella is incredibly flattered by all the attention she’s getting from Brad. She’s told friends he’s always been her No. 1 celebrity crush.”
2018: Jennifer Aniston and Brad Pitt’s Relationship Improves for the Better
February 2018: Jen and Justin announce their split. “It didn’t take long for their different personalities and relationship expectations to clash. They’d fight for weeks at a time!”a source tells Life & Style. Shortly after, Jen leans on her ex-husband Brad Pitt for support.
“What’s surprising about her separation from Justin is that one of her greatest supporters is her first husband,” an insider tells In Touch, adding that Brad “turned out to be a true champion for Jen.”
Another source tells Life & Style, “Brad and Jen have bonded like never before over the past year. And they’ve been helping each other through their respective troubles.” Brad even confessed all of the ways he wronged Jen following their split. “She was left speechless by Brad’s stunning admission. Jen was deeply touched by Brad’s heartfelt words and it has remained on her mind ever since,” the source adds.
April 2018: Jen and Brad reconnect and discuss moving in together. “[Jen] and Brad are ready for the next logical step in their relationship: Moving in together,” a source tells In Touch. “They’ve grown closer in recent months and realize they were meant to be together.”
May 2018: A friend of the couple tells In Touch that Brad and Jen could be looking to start a family! “The two have grown closer over the last couple of years,” the insider says. “His marriage [to Angelina Jolie] fell apart, then her marriage to Justin Theroux ended. During that difficult time, Brad and Jen reconnected. It’s like destiny brought them together, and I can definitely see them having a child together.”